Abstract--The chemical ecology of host-and mate-finding in the pine shoot beetles, Tomicus minor and T. piniperda, was studied in southern Sweden. Beetles were collected in the field from defined attack phases on Scots pine. Using gas chromatography-mass spectroscopy, a number of oxygen-containing monoterpenes, e.g., 3-carene-10-ol, myrtenol, trans-verbenol, and verbenone, were identified from hindgut extracts of both sexes of both species. Compared to T. minor, T. piniperda contained additional compounds and in larger amounts. The amounts were highest in both species at the time when the beetles had bored into contact with the resin-producing xylem-phloem tissue. The synthesis of (1S,6R)-3-carene-10-ol by photooxidation of (+)-(1S,6R)-3-carene is described. In comparative electroantennogram (EAG) measurements on males and females of both species, the most active of the tested compounds was trans-verbenol. Laboratory bioassays of walking beetles showed that T. piniperda was attracted to uninfested.Pine logs. T. minor was more strongly attracted to pine logs infested with females than to uninfested pine logs, indicating a female-produced aggregation pheromone. Field tests confirmed that 7". piniperda was strongly attracted to pine logs. The attraction of T. minor to logs was significant only when logs were combined with racemic trans-verbenol and (1S,6R)-3-carene-10-ol. T. minor was also Coleoptem: Scolytidae. ~This study was made within the project "Odour signals for control of pest insects." 5Present address: VDP Laboratories, P.O. Box 1547, 1200 BM, Hilversum, The Netherlands. attracted to a combination of these monoterpene alcohols alone. We suggest that host and mate location in T. piniperda is achieved by means of a kairomone composed of host monoterpenes, while T. minor utilizes a primitive pheromone synergized by host odors. Evolution of host colonization strategies of the two beetles are discussed.

The crude extract (IPA) of the plant Ipomoea pes-caprae (L.) R. Br. has previously been shown to antagonize smooth muscle contractions induced by several agonists via a non-specific mechanism. Bioassay-guided fractionation of IPA resulted in isolation of the antispasmodically acting isoprenoids beta-damascenone and E-phytol. Their antispasmodic potencies were found to be in the same range as that of papaverine, a general spasmolytic agent. This effect was suggested to play a role in the previously observed anti-inflammatory activity of IPA by interfering with the contraction of endothelial cells. Severe vascular contraction has been shown to be involved in the dermatitis caused by toxic jellyfishes. It is possible that beta-damascenone and E-phytol, by interfering with the contraction of vascular smooth muscle cells, are partly responsible for the previously reported effectiveness of IPA in the treatment of such dermatitis.

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassénii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

Mannich reaction of the propynol (I) yields the amine (IV), which is converted to the precursor (VII).

The crude extract (IPA) of the plant Ipomoea pes-caprae (L.) R. Br. showed an inhibitory effect on prostaglandin synthesis in vitro. Bioassay-guided separation of the extract led to the isolation of four active compounds: 2-hydroxy-4,4,7-trimethyl-1(4H)-naphthalenone (1), (-)-mellein (2), eugenol (3), and 4-vinyl-guaiacol (4). Among the isolated compounds, 3 and 4 were the most active with IC50 values of 9.2 and 18 microM, respectively. For 1 and 2 the IC50 values were 230 and 340 microM, respectively. The influence of 1, 2, 3, and 4 on the formation of prostaglandins may partly explain a previously observed anti-inflammatory effect of the extract IPA.